Raunescine

Details

• Internal ID: c551af00-a8f8-46e1-bf15-680522f0fe76
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl (1R,15S,17R,18R,19S,20S)-18-hydroxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C(=O)OC2CC3CN4CCC5=C(C4CC3C(C2O)C(=O)OC)NC6=CC=CC=C56
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)C(=O)O[C@@H]2C[C@@H]3CN4CCC5=C([C@H]4C[C@@H]3[C@@H]([C@H]2O)C(=O)OC)NC6=CC=CC=C56
• InChI: InChI=1S/C31H36N2O8/c1-37-24-11-16(12-25(38-2)29(24)39-3)30(35)41-23-13-17-15-33-10-9-19-18-7-5-6-8-21(18)32-27(19)22(33)14-20(17)26(28(23)34)31(36)40-4/h5-8,11-12,17,20,22-23,26,28,32,34H,9-10,13-15H2,1-4H3/t17-,20+,22-,23-,26+,28+/m1/s1
• InChI Key: UGMYHMZSPHJQHL-UTYXIPFNSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₆N₂O₈
• Molecular Weight: 564.60 g/mol
• Exact Mass: 564.24716611 g/mol
• Topological Polar Surface Area (TPSA): 120.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.51
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• Raunescine [MI]
• 3,4,5-Trimethoxybenzoyl methyl raunescate
• NSC-72122
• UNII-0063SJ21TG
• 117-73-7
• 0063SJ21TG
• 3beta,20alpha-Yohimban-16beta-carboxylic acid, 17alpha,18beta-dihydroxy-, methyl ester, 18-(3,4,5-trimethoxybenzoate)
• Yohimban-16-carboxylic acid, 17-hydroxy-18-((3,4,5-trimethoxybenzoyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-
• Raunescin
• SCHEMBL7573540
• DTXSID00922238
• NSC72122
• 3,5-Trimethoxybenzoyl methyl raunescate
• Q27231324
• 3.beta., 17.alpha.,18.beta.-dihydroxy-, methyl ester, 18-(3,4,5-trimethoxybenzoate)
• Methyl 17-hydroxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate
• 3.beta.,20.alpha.-Yohimban-16.beta.-carboxylic acid, 17.alpha.,18.beta.-dihydroxy-, methyl ester, 18-(3,4,5-trimethoxybenzoate)
• YOHIMBAN-16-CARBOXYLIC ACID, 17-HYDROXY-18-((3,4,5-TRIMETHOXYBENZOYL)OXY)-, METHYL ESTER, (3.BETA.,16.BETA.,17.ALPHA.,18.BETA.,20.ALPHA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8583	85.83%
Caco-2	-	0.7451	74.51%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.6906	69.06%
OATP2B1 inhibitior	-	0.6443	64.43%
OATP1B1 inhibitior	+	0.7378	73.78%
OATP1B3 inhibitior	-	0.2724	27.24%
MATE1 inhibitior	-	0.8820	88.20%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9314	93.14%
P-glycoprotein inhibitior	+	0.8714	87.14%
P-glycoprotein substrate	+	0.8676	86.76%
CYP3A4 substrate	+	0.7377	73.77%
CYP2C9 substrate	-	0.8421	84.21%
CYP2D6 substrate	+	0.4466	44.66%
CYP3A4 inhibition	-	0.9270	92.70%
CYP2C9 inhibition	-	0.9054	90.54%
CYP2C19 inhibition	-	0.9165	91.65%
CYP2D6 inhibition	-	0.8463	84.63%
CYP1A2 inhibition	-	0.6390	63.90%
CYP2C8 inhibition	+	0.7414	74.14%
CYP inhibitory promiscuity	-	0.8696	86.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5803	58.03%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9570	95.70%
Skin irritation	-	0.7886	78.86%
Skin corrosion	-	0.9526	95.26%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8929	89.29%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.9047	90.47%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.4865	48.65%
Acute Oral Toxicity (c)	II	0.5456	54.56%
Estrogen receptor binding	+	0.8596	85.96%
Androgen receptor binding	+	0.7917	79.17%
Thyroid receptor binding	+	0.5740	57.40%
Glucocorticoid receptor binding	+	0.7830	78.30%
Aromatase binding	+	0.5969	59.69%
PPAR gamma	+	0.7713	77.13%
Honey bee toxicity	-	0.7492	74.92%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5451	54.51%
Fish aquatic toxicity	+	0.7032	70.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4302	P08183	P-glycoprotein 1	99.72%	92.98%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.71%	96.09%
CHEMBL2535	P11166	Glucose transporter	98.68%	98.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.92%	91.11%
CHEMBL1914	P06276	Butyrylcholinesterase	97.69%	95.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.86%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.10%	85.14%
CHEMBL2581	P07339	Cathepsin D	90.65%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.53%	93.99%
CHEMBL5747	Q92793	CREB-binding protein	88.07%	95.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.71%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.36%	99.17%
CHEMBL5028	O14672	ADAM10	86.04%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.36%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.34%	94.00%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.60%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.25%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.13%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	81.12%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.01%	97.09%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	80.60%	97.03%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.54%	90.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.36%	94.08%

Plants that contains it

• Aegiceras corniculatum
• Rauvolfia serpentina
• Rauvolfia verticillata

Cross-Links

• PubChem: 251566
• NPASS: NPC303096
• LOTUS: LTS0271113
• wikiData: Q27231324